Organocatalyzed Transient Dienamine-Mediated Diels-Alder Reactions between α,β-Unsaturated Ketones and Alkenes

Title:Organocatalyzed Transient Dienamine-Mediated Diels-Alder Reactions between α,β-Unsaturated Ketones and Alkenes

Volume: 15 Issue: 5

Author(s): Iosune Arrastia, Ana Arrieta and Fernando P. Cossio*

Affiliation:

• Donostia International Physics Center, San Sebastian/Donostia,Spain

Keywords: Organocatalysis, diels-Alder reactions, cycloadditions, michael additions, pericyclic reactions, stepwise mechanisms.

Abstract: Organocatalyzed (4+2) cycloadditions (Diels-Alder reactions) are reviewed in this manuscript. Among the different catalytic alternatives, reactions involving α,β-unsaturated ketones and alkenes are considered. In these processes, substituted cyclohexanones are obtained via HOMO activation generated by amine organocatalysis that generate transient dienamine species. Both concerted and stepwise mechanisms are described. In most cases, excellent regio-, diastereo- and enantiocontrol have been observed.

Cite this article as:

Arrastia Iosune, Arrieta Ana and Cossio P. Fernando*, Organocatalyzed Transient Dienamine-Mediated Diels-Alder Reactions between α,β-Unsaturated Ketones and Alkenes, Letters in Organic Chemistry 2018; 15 (5) . https://dx.doi.org/10.2174/1570178615666180102144530